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1.
When a womans vagina has been "used" to such a great extend that it now appears as flabby flesh flaps, similar to roast beef. Hence the 5 for 5 deal at Arby's where you get your fair share of roast beer for a nominal price.
Set the stage as one buddy to another after the successful conquest of a ripe young woman.

Johnny: "So yeah, I hit that last night"
Sam: "How was she, 5 for 5?"
Johnny : "Naw man (pleasant smile) it was like 1 for 99 cent!"

From this dialog Johnny and Sam were able to share information without hurting anyones feelings.
by Joey (Credit to BeanWack) September 19, 2006
 
2.
5 24oz Beers for 5 Dollars. AKA getting shwasted for $5
Yo man, Im feelin a 5 for 5.
by istoleyourboat August 09, 2011